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Hi first time Omni user here, but computer and IT literate so I'm a little stumped here.

I've just purchased OmniFocus for my Mac and iPhone and I have a bone to pick with the OmniFocus/OmniSync/Calendar integration system.

I easily managed to get my subscribed calendar functioning and events show up in under a minute (just like the website and forums say they should).

I have an issue though that none of my actions that have due dates more than 14 days in the future don't sync over to the subscribed calendar?!?!?!?!?!? So if it is the 10th of January actions that are due beyond 11:59PM on January 24th don't show up!

they are syncing fine to the the phone and from the phone to the computer. They just refuse to transfer to the subscribed .ics file.

I've connected to the OmniSync server and downloaded the .ics file to make sure that they are making it to the file alright, but it only contains 14 days worth of events.

I really wish this is something I knew BEFORE spending $100! I work on several projects that are 4 months+ in length and I like all my events to be in my calendar (even if they are likely to change in the future).

You're misunderstanding the purpose of that feature. It's a relic, present because Apple didn't provide a way for iOS applications to send local notifications at one time. Someone at Omni realized that if they stuffed 0-length events in a calendar, that the iOS calendar app would put up notifications and so those who wanted a warning that something was about to be due could have them without needing internet connectivity. Only 14 days of events are populated to keep the process speedy.

There are some scripts floating around on the OmniFocus Extras forum that may be of use to you in trying to populate your calendar with everything you've got in OmniFocus.

Exporting your tasks to the calendar is a mixed blessing, I've written a tool that does it (ofexport) and Rob Trew I think has a more friendly and interactive AppleScript.

The problem is how to map your tasks into the calendar. A naive approach is to use the start/due dates from OF but the results look bad and it's easy scatter a bazillion trivial entries all over your calendar and make it utterly unusable.

A task that starts on Monday at 9am and is due on Friday at 6pm would essentially colour in your entire week. If you have several of those your calendar becomes pretty nasty.

There are ways to deal with that but I'm still wrestling with what the right approach is. The best I've managed to come up with is a bit of a compromise.